Specificity of chemiluminescence in the metabolism of benzo[a]pyrene to its carcinogenic diol epoxide.
The metabolism of 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene results primarily in the ultimate carcinogenic metabolite of benzo[a]pyrene, 7,8-dihydroxy-9,10-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene and to a lesser extent 7,8-dihydroxy-9,10-dioxetane-7,8,9,10-tetrahydrobenzo[a]pyrene, from which chemiluminescence is observed. This specific microsomal chemiluminescence has been used to establish that the rate-limiting reaction in the metabolism of benzo[a]pyrene to the bay region diol epoxide is the production of the 7,8-diol. The microsome-mediated chemiluminescence of the parent benzo[a]pyrene is therefore an indicator of the activity of the specific sequence of metabolic reactions leading to the ultimate carcinogenic metabolite.
D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide; D000818:Animals; D001580:Benzopyrenes / Q000378:metabolism*; D007700:Kinetics; D008163:Luminescent Measurements; D008748:Methylcholanthrene / Q000494:pharmacology; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D051381:Rats; D013329:Structure-Activity Relationship
D001580:Benzopyrenes; D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide; D008748:Methylcholanthrene